Medium-sized cyclophanes. Part 18. 5-tert-Butyl-8-substituted [2.2]metaparacyclophanes: preparation, X-Ray diffraction studies, and their treatment with Lewis acids in benzene
Medium-sized cyclophanes. Part 18. 5-tert-Butyl-8-substituted [2.2]metaparacyclophanes: preparation, X-Ray diffraction studies, and their treatment with Lewis acids in benzene
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中型环芳烷。
DOI：
10.1039/p19920002675
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发表时间：
1992
期刊：
影响因子：
--
通讯作者：
M. Tashiro
中科院分区：
文献类型：
--
作者：
T. Yamato;J. Matsumoto;K. Tokuhisa;K. Tsuji;K. Suehiro;M. Tashiro
本文报道了用硫法合成各种8-取代的5-叔丁基[2.2]间对环蕃8，并对双硫杂[3.3]间对环蕃6和8-甲基[2.2]间对环蕃1b进行了X-射线衍射研究。AlCl 3-MeNO 2催化的8-烷基-和8-羟基-5-叔丁基[2.2]间对环芳8在苯中的反式叔丁基化反应以良好的产率得到所需的8-烷基-和8-羟基[2.2]间对环芳1。然而，5-叔丁基-8-甲氧基[2.2]间对环芳烷8 c异构化为无应变的5-叔丁基-8-甲氧基[2.2]间环芳烷13，并将其转化为四氢芘11和12。并对反应机理进行了讨论。
The preparation of various 8-substituted 5-tert-butyl[2.2]metaparacyclophanes 8 using the sulfur method, and X-ray diffraction studies of dithia[3.3]metaparacyclophanes 6 and 8-methyl[2.2]metaparacyclophane 1b, are described. AlCl3–MeNO2-catalysed trans-tert-butylation of 8-alkyl- and 8-hydroxy-5-tert-butyl[2.2]metaparacyclophanes 8 in benzene gave the desired 8-alkyl- and 8-hydroxy[2.2]metaparacyclophanes 1 in good yield. However, 5-tert-butyl-8-methoxy[2.2]metaparacyclophane 8c was isomerized to the strainless 5-tert-butyl-8-methoxy[2.2]metacyclophane 13 and this was converted into the tetrahydropyrenes 11 and 12. The mechanism of this reaction is also discussed.